Real Estate Investment Properties for Sale in Chester, MD

Looking for investment property in Chester, MD with high ROI ?

Explore a variety of short-term homes & houses in Chester, MD. Invest wisely with VRBO & Chester, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Condos for Sale in Chester, MD

Search for Condo for Sale in Chester, Maryland. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 12 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
34-E QUEEN ANNE Way CHESTER, MD Price Improvement on this CHESTER RIVER WATERFRONT Eastern Shore! Nestled within the water...	2 beds \| 3 baths \| 1,104 sq.ft.	$469,000	Airbnb cash on cash: 6% Traditional cash on cash: 4.56% Airbnb Rental Income: $4662 Traditional Rental Income: $3067 Airbnb ROI: 6% Traditional ROI: 4.56%
312 BLENNY Lane CHESTER, MD You do not want to miss this opportunity to enjoy island living in this maintenance free, ...	3 beds \| 4 baths \| 1,899 sq.ft.	$479,000	Airbnb cash on cash: 9.44% Traditional cash on cash: 4.77% Airbnb Rental Income: $6279 Traditional Rental Income: $2950 Airbnb ROI: 9.44% Traditional ROI: 4.77%
141 SWITCHGRASS Way unit: 34 #34 CHESTER, MD ** NICE VIEWS OF THE CHESTER RIVER * LOWEST PRICED SEVERN MODEL** K Hovnanian'...	3 beds \| 3 baths \| 2,600 sq.ft.	$684,950	Airbnb cash on cash: 5.57% Traditional cash on cash: 2.44% Airbnb Rental Income: $6279 Traditional Rental Income: $3044 Airbnb ROI: 5.57% Traditional ROI: 2.44%
170 HARRIER WAY #34 CHESTER, MD Just reduced by $55,000 to $740,000 with immediate availability. Open House this Sunday 9/...	3 beds \| 3 baths \| N/A	$740,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 2.47% Airbnb Rental Income: $6279 Traditional Rental Income: $2981 Airbnb ROI: 5.46% Traditional ROI: 2.47%
170 HARRIER Way unit: 11 #11 CHESTER, MD Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bed...	2 beds \| 3 baths \| 2,003 sq.ft.	$499,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 4.02% Airbnb Rental Income: $4662 Traditional Rental Income: $3099 Airbnb ROI: 5.3% Traditional ROI: 4.02%
190 HARRIER Way unit: 11 #11 CHESTER, MD Luxury 55+ Living at Four Seasons on Kent Island - Move-In Ready & Priced to Sell! Welcome...	2 beds \| 3 baths \| 2,003 sq.ft.	$540,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 2.17% Airbnb Rental Income: $4662 Traditional Rental Income: $2354 Airbnb ROI: 4.83% Traditional ROI: 2.17%
1000 HERONS NEST Way unit: 32 #32 CHESTER, MD Move in this May and enjoy low-maintenance living in the sought-after 55+ community of Fou...	2 beds \| 2 baths \| N/A	$499,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 2.75% Airbnb Rental Income: $4662 Traditional Rental Income: $2521 Airbnb ROI: 5.26% Traditional ROI: 2.75%
47-D QUEEN ANNE Way CHESTER, MD New Price- Owner has relocated & says sell it! Enjoy resort style living every day in the ...	2 beds \| 3 baths \| 1,550 sq.ft.	$555,000	Airbnb cash on cash: 5.39% Traditional cash on cash: 2.23% Airbnb Rental Income: $4662 Traditional Rental Income: $2059 Airbnb ROI: 5.39% Traditional ROI: 2.23%
1000 HERONS NEST Way unit: 22 #22 CHESTER, MD Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum C...	2 beds \| 3 baths \| 1,900 sq.ft.	$488,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.47% Airbnb Rental Income: $4662 Traditional Rental Income: $3249 Airbnb ROI: 5.44% Traditional ROI: 4.47%
108 BODYS NECK Road CHESTER, MD Experience Autumn Serenity on the Waterfront Discover the perfect blend of coastal charm a...	3 beds \| 3 baths \| 1,791 sq.ft.	$499,900	Airbnb cash on cash: 8.88% Traditional cash on cash: 4.8% Airbnb Rental Income: $6279 Traditional Rental Income: $3136 Airbnb ROI: 8.88% Traditional ROI: 4.8%
807 AUCKLAND Way CHESTER, MD PRICE REDUCED! Waterside Living on Kent Island! Discover the perfect blend of comfort and ...	3 beds \| 4 baths \| 2,100 sq.ft.	$455,000	Airbnb cash on cash: 9.84% Traditional cash on cash: 6.18% Airbnb Rental Income: $6279 Traditional Rental Income: $3486 Airbnb ROI: 9.84% Traditional ROI: 6.18%
30-C QUEEN MARY Court CHESTER, MD Enjoy low-maintenance living in the desirable waterfront community of Queen's Landing, off...	2 beds \| 3 baths \| 1,440 sq.ft.	$339,900	Airbnb cash on cash: 9.59% Traditional cash on cash: 5.9% Airbnb Rental Income: $4662 Traditional Rental Income: $2518 Airbnb ROI: 9.59% Traditional ROI: 5.9%

Your search for investment property begins and ends here

Condos for Sale in Chester, MD

34-E QUEEN ANNE Way

CHESTER, MD

2 beds | 3 baths | 1,104 sq.ft.

$469,000

Airbnb cash on cash: 6%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $4662

Traditional Rental Income: $3067

Airbnb ROI: 6%

Traditional ROI: 4.56%

312 BLENNY Lane

CHESTER, MD

3 beds | 4 baths | 1,899 sq.ft.

$479,000

Airbnb cash on cash: 9.44%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $6279

Traditional Rental Income: $2950

Airbnb ROI: 9.44%

Traditional ROI: 4.77%

141 SWITCHGRASS Way unit: 34 #34

CHESTER, MD

3 beds | 3 baths | 2,600 sq.ft.

$684,950

Airbnb cash on cash: 5.57%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $6279

Traditional Rental Income: $3044

Airbnb ROI: 5.57%

Traditional ROI: 2.44%

170 HARRIER WAY #34

CHESTER, MD

3 beds | 3 baths | N/A

$740,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $6279

Traditional Rental Income: $2981

Airbnb ROI: 5.46%

Traditional ROI: 2.47%

170 HARRIER Way unit: 11 #11

CHESTER, MD

2 beds | 3 baths | 2,003 sq.ft.

$499,000

Airbnb cash on cash: 5.3%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $4662

Traditional Rental Income: $3099

Airbnb ROI: 5.3%

Traditional ROI: 4.02%

190 HARRIER Way unit: 11 #11

CHESTER, MD

2 beds | 3 baths | 2,003 sq.ft.

$540,000

Airbnb cash on cash: 4.83%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $4662

Traditional Rental Income: $2354

Airbnb ROI: 4.83%

Traditional ROI: 2.17%

1000 HERONS NEST Way unit: 32 #32

CHESTER, MD

2 beds | 2 baths | N/A

$499,000

Airbnb cash on cash: 5.26%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $4662

Traditional Rental Income: $2521

Airbnb ROI: 5.26%

Traditional ROI: 2.75%

47-D QUEEN ANNE Way

CHESTER, MD

2 beds | 3 baths | 1,550 sq.ft.

$555,000

Airbnb cash on cash: 5.39%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $4662

Traditional Rental Income: $2059

Airbnb ROI: 5.39%